


The underwear drawer

by MoonlightIcarus



Series: Bobby Tries New Things [4]
Category: Supernatural
Genre: Anal Fingering, Anal Plug, Anal Sex, Barebacking, Beards (Facial Hair), Body Hair, Coming Untouched, Domestic, Face-Sitting, Fluff, Groping, Jock Straps, M/M, Mutual Masturbation, Oral Sex, Porn With Plot, Public Display of Affection, Rimming, Smut, Speedos, Underwear Kink, hot bear on bear action
Language: English
Status: Completed
Published: 2019-10-04
Updated: 2019-10-04
Packaged: 2020-11-23 12:54:41
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 7
Words: 18,436
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20892440
Author URL: https://archiveofourown.org/users/MoonlightIcarus/pseuds/MoonlightIcarus
Summary: Crowley is tired of Bobby always wearing his boring old shapeless boxers and decides to change that. Of course being Crowley he does it without Bobby's permission but that's never stopped him before. Now he's going to see how far he can take it.





	1. Boxers

Crowley had just finished inside of that nice tight ass and was enjoying his after glow when Bobby had to get up to go clean himself up in his bathroom. When he came back out he went to the top drawer of his dresser and pulled out a pair of his boxers to sleep in much to Crowley's dismay. He didn't mind that Bobby got out of bed he actually quite liked the wonderful view of that nice furry rump. No the issue came with what Bobby was putting on it. It was this horribly shaped pair of boxers that ballooned out like clown pants and had a button on the fly. They covered everything from waistline to the knee. These were the kind that most stores didn't even carry anymore. You would have to go to an arms surplus store and buy them there and they were the only kind of pants that his redneck chose to wear.

"You know you could go and clean yourself up like a normal person," Bobby nagged as he slid into bed next to his demon. Using his shoulder as a pillow.

"Love did you forget I'm not a person, I'm the king of hell?" He could feel those tasteless undergarments pressed up against his thigh. Crowley loved the big bear of a man but everyone had their faults. So as Bobby started to drift off to sleep Crowley started formulating a plan.

....

Crowley had been nagging Bobby to sleep more and to the surprise of both of them he was. Granted at least part of that was attributed to the previous night full of hard core fucking but sleep was still sleep. So at 7:00 am the plan was in motion.

This was not quite what he expected. Of course Crowley knew he would have to start off small and ease Bobby into something better but standing in the mens underwear section of a superstore at 7:05 was certainly killing the romantic atmosphere in his head. He was looking for something nice but not dramatic. And while he could have simply created a pair he needed something authentic to start out with. Eventually settling on a four pack mesh boxer set. It took very little time to find the right size after all Crowley was very familiar with that part if Bobby's anatomy.

The checkout was to be expected. One lone cashier looking dead in the eyes given the time. He chose to forgo the plastic bag (humans may be killing the planet but this demon wouldn't add to it) and went outside. Warping home as soon as he was out of the cameras line of sight.

Back at the house he opened the package and went about replacing all of the current pairs of pants in the top drawer with these new better ones. All the while removing the old pairs to be properly disposed of.

....

When Bobby woke up he realized three things he was thirsty, he was sore, and his ass fucking hurt. All the normal signs of a night spent with Crowley. He did the first thing all civilized people do when they wake up in the morning and took a shower. He took care to scrub away all the grime from sex that he was too tired to deal with last night. Carefully shampooing his whole body because as Crowly put it,"I love your nice soft hair and almost all of you is covered in hair." Once done with his thorough rinse he carefully dried off to avoid soaking his bedroom carpet.

Walking into his bedroom with his towel still around his shoulders he made his way to the top drawer of his dresser and was quite surprised with what he found. In place of his usual army standard boxer he found four pairs of mesh underwear all in annoyingly bright colors. There was one explanation to this and his name was Crowley.

Bobby knew he had to pick a pair to wear because going to confront the demon naked would only please Crowley more, and also because he was never someone who enjoyed going commando.

He surveyed his options. He had fire engine red, something so yellow it put lemons to shame, neon green, and electric blue. He eventually decided on the red pair and started shimmying them up his legs. He did have to admit that the mesh felt rather nice on his legs and he liked how the thick waistband sat on his hips. Plus they still went down to the knee so he didnt feel exposed, but they also had a pouch in the front so he felt like the whole world could see his dick.

Putting his inabitions aside he threw on a white tee shirt and decided to go confront Crowley about this now. He could hear noise in the kitchen wanted to settle this before it escalated.

"Crowley can you please explain yourself," he announced walking into the kitchen.

"What is there to explain love I haven't changed though I see your pants certainly have," while saying this he went and wrapped his arms around Bobby's torso and set his head on one of his shoulders.

"Well then could you please explain where my underwear went and why it was replaced with the neon vomit?"

"Love I don't expect much from redneck fashion but I was simply growing tired of your boring army standard boxers. I want to be able to see this big arse more," he chose to emphasize his point by moving his hands to squeeze Bobby's arse through his underwear and then quickly moved his hands to slowly stroke around those nice thighs occasionally ghosting over the front.

"And what if I liked my army standards over these briefs."

"They are still boxers, they're just mesh and fitted now. And I would say you are enjoying these based on the was you keep rubbing your thighs together and the large tent you've set up in the front," At this Bobby looked down and was surprised to see his erection straining through the mesh.

Crowley then grabbed the nice big cock through the boxers and started lazily stroking it. Bobby's hands went up and behind his head to grasp at the demons short hair. The pose left Bobby so exposed and Crowley took advantage if it by using his free hand to pinch the left nipple all while rutting up against the back of the boxers.

He just kept lazily stroking, thrusting, and teasing through his clothes. Ocassionally Bobby would clench his hands in that short hair but aside from that he just let out short huffs. Growing bored of the languid pace he set Crowley went to bite at that exposed neck. Being just light enough to avoid drawing blood and then sucking and licking it to make it grow big and dark. He wanted everyone to see it. Showing who was fucking the famous hunter Bobby Singer. This made Bobby let down his guard even more and Crowley was fully ready to capitalize on this moment. Removing his hand from the nipple he moved it to the hem of that white tee shirt and then rucked it up for some skin on skin contact. This time choosing to torment his other nipple. Pinching and teasing it.

Crowley took in the big expanse of the exposed stomach and chest. The stocky belly slowly getting damp with sweat. That chest that seemed to always stay at least partially toned. And his guilty pleasure for love handles. Perfect for groping in bed or maneuvering his lover just how he wanted them. Every inch was worn and covered in that hair making Bobby the perfect example of a bear. That light brown hair alone drove him insane. The way it covered his pecs and spiraled around his pink nipples. It covered his stomate in a nice even thick layer completely encompassing it to where you couldn't even see the skin and it made a lovely contrast to the exposed areas on his body. It continued onto his sides and back gradually thinning and framing his whole body. He enjoyed how it added texture to those nice shoulders and arms. The way it went down his calves and thighs matching all around his nice legs. He was also glad the hunter had a good thick bush in the front it continued the hair on his stomach but was even thicker while still maintaining that lovely brown color. It gave him something to play with and tease before moving onto that nice cock. And whenever he would deep throat Bobby his nose was buried in it and it gave off a heady sent of musk. And that big perfect arse. It was where his love was by far the palest and the splash of color made it look all the better. He liked when it would tangle with his beard as he ate Bobby out. Along with that it just made the view all the more special, noone had an arse that perfect with a precise covering of hair.

He adored how exposed the usually gruff hunter was and all of this was just for him too see. Wanting to draw this out and listen to all the huffs and moans that Bobby made he kept on slowly thrusting up against that clothed ass. Making sure there was never enough pressure to actually get Bobby off.

When all he could hear were short quick puffs of breath he decided maybe it was time to finish this. He let go of that cock and reached into the boxers to grasp it and squeeze it directly. Simultaneously he punished that nipple hard, sucked on that hickey he made, and ground into that firm rump. The sudden change in stimulus lead to a strangled growl as Bobby came inside his new underwear.

"Was this your plan?" Bobby was still huffing in the wake of his impromptu orgasm.

"Not quite darling," the grin was audible in his speech, "While I certainly wanted to enjoy looking at this nice arse in some actual fitted clothing I also want to see you in all manner of pants. To put it frankly I want to fuck you in your underwear," his voice was dead serious even as he moved his arms back around that nice torse.

"Fuck, fine. I know I'm going to regret this but fine we can try this weird thing you want. But just so you know no stockings, panties, or maid outfits."

"Wouldnt dream of it I dont want you looking like a Victorious Secret model. I like you because you look like a man's man. I much prefer the idea of you parading around the house in some pants that emphasize your best assets or you coming home from a hunt and being so desperate you can't even get your pants of before I fuck you. Oh and one last thing love. Not only did you ruin this front but I took the liberty to mark the back," he kissed the side if Bobby's dead and disappeared.

Reaching back Bobby towards the back of the boxers and felt the wet stain. The fucker was naked the entire time.


	2. Trunks

**Summary for the Chapter:**

> Bobby shows some skin and Crowley gets to watch

It had been three days and Crowley had made no indication of returning Bobby's old underwear. This would be less of an issue if Crowley didn't appear for sex the moment Bobby got dressed or changed. He always had different ideas of how to ruin Bobby's new underwear and somehow none of it involved penetration.

That leads to now, where Bobby just got out of the shower without any clean underwear that he is aware of but since this is the morally ambiguous king of hell he's dealing with it seems necessary to check his top drawer anyway. What he finds as he pulls it open is certainly unexpected. Inside are seversl brightly colored briefs that look like they will cover all of an inch of his thigh. Each one has a different but equally loud and absurd pattern on them. At the very least the boxers were one solid color. Bobby can tell one is supposed to be palm leaves with a back ground of a pastel sky. Given the choices none seem significantly better than the others so he goes with that pair.

The moment they rest on his hips Crowley appears behind him, "Hello darling. What do you think of the new trunks?"

"Trunks?"

"Yes trunks their like boxer briefs but shorter. I didnt see a need for you to try boxer briefs when you were going to try these eventually. It just seemed like a redundant step. Besides now I get to se more of those delicious thighs," He was licking his lips staring at the way Bobby slightly spread his legs when he sat on the bed still going topless.

"And do all trunks come in such ugly patterns. It's like a fucking travel banner on my ass," he crossed his arms over his chest in actual annoyance with Crowley's shenanigans.

"Yes love that's the point. They're made to draw people's attention. But of course these will only draw my attention since I know you would never wear them where someone could actually see you."

"Don't you have demons to abuse or something so I can actually work today. I haven't been able to do anything because of you're neverending neediness," The whole time Crowley never removed his eyes from Bobby's crotch and Bobby could feel the way the trunks started to ride up between his legs emphasizing his dick even more.

"Fine. Fine. I'll leave you be for now. Call if you need anything," he leaned in for a kiss, "and don't have too much fun without me," he squeezed Bobby's dick and disappeared before he could react.

....

It was amazing what someone could accomplish when they aren't constantly pleasing a demon desperate for attention with an endless sex drive. He did his research, translated ancient manuscripts, and faked being a government official so all in all a very productive day.

"How would he like it if interrupted him every seven minutes to have sex." And with that thought Bobby had a slightly devious but entirely justified idea and the best part was it would only take minimal effort to set up.

....

Once everything was good to go he called Crowley saying he needed help with a demonic translation. The demon so graciously appeared not ten minutes later in the kitchen to greet him.

"Love why are you in the kitchen if you need help with a translation?"

"I didn't know how long you would take, I was thirsty, and my liver can only do so much after a life of stress and binge drinking."

"You know I could always get you a new liver if this one gives out on you."

"I'll remember that now come on and help me with this so you can get back to your torture and gloating," Bobby started walking back to the library.

Following him close behind Crowley called, "It's not gloating when you're disciplining your subjects."

Bobby had just crossed the threshold to the library but Crowley was stuck in his tracks. "The hell is this," He looked to Bobby who just pointed at the ceiling above him. Following that hand he saw it, a demon trap painted on the ceiling above him. "And may I ask why you're doing this?"

"I'll explain," bobby started taking off his shoes, "I got tired of you constantly coming in and stopping me from working," He kicked the shoes and socks away, "I never have time to actually do my research with all the sex you demand," he removed his jacket and top shirt leaving his upper body in just a faded wifebeater, "But I knew I couldn't just interrupt you and have sex because you would enjoy that too much," he now started on his belt and was lowering his jeans. "So I decided I'd have you watch me enjoy my self to interrupt your work but I'd still keep you from enjoying it."

Now standing in just his tropical neon underwear and wifebeater be went to learn over his desk, spreading his legs to give Crowley a perfect view of what he couldn't have. "So enjoy the show if you can."

He then reached into his trunks and pulled out his dick already hard from the slow stripping as well as the sensual rub of his underwear against his body. He pulled his dick out and angled it so Crowley could see the tip between his spread legs. Bobby was well aware the Demon could simple touch himself but it would be so much less pleasant than the sex he was accustomed to.

He used a slow languid pace as he stroked himself. In this position he could feel the trunks starting to slide up his ass but he honestly didn't care, all the more torture towards Crowley. He let out a long sigh as the smeared his precome over his cock and kept getting more and more to properly lube himself up.

....

Crowley stood dumbfounded at the sight of Robert Singer bending over like a cheap whore and exposing the whole outline of his arse through theose glorious trunks. He moaned loudly on each upstroak and Crowley could just see the tip of his dick and his fist from this position. When Robert stated to slightly shake his ass he lost it and pulled himself into his hand. Starting off at a brutal pace to finish fast. He stilled when he heard a loud moaned "Idjit," and saw the streaks of white paint the floor. Robert then turned around and left himself on display for Crowley eyes only. He leaned back on his desk with his legs still spread apart, and his chest was heaving from the exertion. He hadn't even bothered to tuck himself back into his pants. It was enough to send him over the edge even after such little stimulation.

Once the after glow faded Bobby broke the silence, "Just because you came to that doesn't mean I'm letting you out so soon."

**Notes for the Chapter:**

> Up next Briefs


	3. Briefs

**Summary for the Chapter:**

> A relaxing day at home. Well it depends on your definition of relaxing.
> 
> Chapter 3 is now bigger, longer, and uncut.

He was just beginning to shake off that lazy feeling of sleep when he registered the warm body still pressed up against him. It really was quite odd. Usually Crowley was gone by morning either to make breakfast or due to his never ending responsibilities as the king of hell. So it was a pleasant surprise to still have his company in the wee hours of the morning. Of course that peace was quickly disturbed by Crowley talking.

"You know love we could just stay in today, ignore work, and relax," He was snuggling up against Bobby's side to try and sell the idea. He even started kissing his shoulder to really sell it.

Groaning to clear his throat of the morning grogginess, "As wonderful as that sounds I know you have something else planned and I'm not entirely sure that I will like it," Bobby was starting to roll over onto his back so he could sit up for this conversation.

"Well I did want to continue out little experience, but I wasn't planning anything monstrously different for the day."

"And what is your plan you little cretin." He was only partially teasing after all he was still annoyed with how Crowley killed the mood.

"How about I tell you after you shower and get washed up. You are still a bit grimy from our fun last night," 

Crowley didn't like commenting on his hygiene but something had to be done. Sex was a great look on Robert but certainly not an ideal fragrance.

Bobby moved to climb out of his bed and felt this back pop more times than he felt comfortable acknowledging. "I'm going ya idjit, but please don't break anything. And no please don't respond I really can't bicker with you this early in the day. Feel free to be smart after I've bathed and eaten something. Hell, just let me drink something strong and I'll be good to go," He had locked the bathroom door before Crowley got the chance to respond. He took off his trunks (these ones were about five shades of bright pink with a neon yellow waist band - there was a reason Bobby waited to wear these last) and turned the water to nearly scalding to settle his old joints. The shampoo and body wash were amazing on his skin. Removing that layer of filth that he ended up sleeping in all night. It was something he never liked thinking about but he knew it would never change. He was just too tired after sex to clean himself well.

Once he felt clean enough and was sure that he'd used enough hot water he took the towel off the pole next to the shower and went to go get dressed. He was seriously starting to consider putting hardwood in his bedroom to avoid the tedium of thoroughly drying off. Not to mention how much trouble he went through cleaning his cum off the library rug. Sure it had been worth it, but balls did it take too much effort to scrub out. Reaching his dresser he open his top drawer to find only one garment inside. A single pair is pristine white briefs. These were not your standard Fruit of the Loom or Hanes white briefs, no these were much higher cut and would leave all of his thighs exposed, more shaped in the back so at least part of his ass would be on display, and finally how the part connecting the front and back was only about an inch wide, if that, meaning if he spread is legs too much everything could fall right out. Worst still was that Bobby realized that all his drawers were empty, he only had this one pair to wear.

"Crowley!" He shouted loud enough that the fucker would hear him no matter where he was in the house.

"Yes love? Oh I see you've found today's newest challenge. Don't worry I'll give all you're clothes back later and you won't be wearing just that," Everything was said so innocently but even a toddler could tell he wasn't being genuine.

"If it's bunny ears I will stab you."

"Oh no sweetheart just this," And there in Crowley's hand appeared a set of equally nice suspenders. They even appeared to be made of the same material as waistband on the briefs.

Bobby knew he would agree but it only seemed fair that he too get something out of this little escapade.  
"Fine ill wear it," Crowley's face look positively giddy, "However you have to wear the same thing but in red."

"Deal," Crowley responded far too quickly.

"You know for a demon you should let someone finish when making a deal. Wear the same thing in red and an anal plug with a devils tail on it," His voice was so smug in that moment it would put Lucifer to same.

"Deal," Crowley said with all seriousness in his voice. He snapped and a second matching set appeared on the bed next to wear Bobby threw his briefs. "Now love time to get dressed after all we have a whole day of nothing but relaxation ahead of us," It almost seemed like a waste to get dressed because they both knew they would be getting undressed so shortly after this.

They both started with the briefs. Bobby had no idea what the material actually was but it felt like nirvana on his skin. He also noticed how even though the waist band sat high enough to cover his whole ass it covered significantly less in the front covering just a little above his dick and almost all of his thighs could be seen by the world, but his fear of indescent exposure was alleviated since the briefs were too tight for something to slip out. "I see you noticed the style. It's made to accentuate all your best assets. Now allow me to help you with the suspenders they're supposed to be set a certain way."

He clipped the suspenders on the front of the waistband and pulled it over Bobby's head so the straps went directly over his exposed nipples and then they crossed eachother on the center his back, and finally snapped onto the back of the waistband. The suspenders were tight but didn't pull on the underwear instead it put light tension on his shoulders and Bobby could feel that every time he moved it would aggravate his extremely sensitive nipples. Feeling the soft almost silky material on his skin he turned to Crowley to see him dressed in much the same way with the red highlighting the black hair adorning his entire body from his feet to his calves and thighs to the surprisingly lean stomach and muscular chest. He was still a nice stocky man but it suited him well.

Bobby again was interrupted from his thoughts and moment of peace. "So love how about we head down stairs and enjoy this beautiful day."

"Aren't you forgetting something? A devilish little something?" Crowley was clearly banking on Bobby forgetting but he learned to never forget anything when dealing with a demon no matter how casual the situation was.

"Truly nothing escapes the mind of Robert Singer," He then snapped and a red devil tail appeared out of the back of the briefs. It was just about three millimeters thick and would have been a little over a foot long when fully stretched out but currently it was curved into an S shape with the tip resting a little above the waistband and it pointed outward.

"The deal was a plug."

"It is, you can come and feel it for yourself," he placed himself right in Robert's arms and moved one hand into the back of his briefs to touch his ass and feel for the plug. When Bobby's hand reached the tail he pulled a little and felt the resistance form Crowley's ass. "See something right up my arse just like you asked now lets go enjoy ourselves.

....

They spend most of the day on Bobby's old couch watching Reruns and old movies. Bobby sat on one end of the couch with one leg up and the other leg crossed over it. Due to the plug Crowley spent most of the day stretched out along the couch on his stomach or his side with his head resting oh Bobby's thigh and his legs thrown over the open arm of the couch. Occasionally he got up to get food or some drinks for them because they both knew if Bobby did he would get too turned on by the feel of the suspenders on his sensitive skin. Even the little bit he moved on the couch left a noticeable bulge in his briefs. The white stretching to accommodate his girth. This was nothing compared to what he saw on Crowley. The way the suspenders were tight over that surprisingly muscular back or how his ass was clearly defined by the skin tight briefs and were even riding up a little. Even the flush of his chest and neck matched the red of the suspenders perfectly. And to top it all off the monster cock Crowley had was absolutely obscene. He could occasionally see the tip poking out of the top or the underside being exposed from how much the front was stretching. And now Bobby knew for sure that Crowley fell to the right.

Eventually though he had to pee like a horse and got up from the couch to do his business. As he got up Crowley was perched on the edge of the couch to avoid putting too much pressure on the plug, but that thought left his mind when he saw his dear Robert walking around. Throughout the day he only got sparing glances as that perfect arse in those sinfully small briefs but now he was getting one long extended view. Then when Bobby went to take the stairs he didn't just get to see that sinful giggle but also heard the poorly covered up gasp as his nipples were tortured by the contact of shift on each step. It was time to take a more active approach.

....

When Bobby came back down the stair he had to focus on not over reacting to that wonderful feeling in his chest. Hitting the ground floor he saw that the coffee table had been cleaned of all the cups and plates from earlier in the day and he could hear the water running in the kitchen sink. Deciding to wait for Crowley to return he laid back on the couch with his head resting on one arm and his legs thrown over on the other. If felt nice to let his body stretch out and take in the feeling all over his skin. If these were any softer he could just wiggle around in them until he eventually got off.

Shortly thereafter Crowley came back into the room. "So I decided what we should watch next," Crowley said as he forced Bobby to sit up again.

"And what would that be?" Crowley had made very few suggestions throughout the day and the ones he had made were all classics like Casablanca or 12 Angry Men so he was curious what this new suggestion was.

"Cheap gay 90s porn," he said it straight faced.

"Wait what?" This was still the overly posh king of hell right? He wouldn't possibly suggest...

"I said cheap gay 90s porn. Any objections?" Crowley had now moved to sit on the couch

"Why would I want to watch cheap porn and why would you want to watch it with me?"

Kneeling on Bobby's open side and leaning right against his ear, "Because I'm going to blow you with it in the back ground. Any objections?" Of course Bobby was too dumbfounded to respond. "Since I hear no objections I'll take that as a yes."

Crowley snapped and some grainy smut came on the tv but Bobby was far more interested with the way Crowley moved to kneel on the floor between his legs and moved both of Bobby's over his shoulders so Crowley was boxed in by him. He reached toward the tight briefs and pulled that lovely cock right out of the trapdoor hole in the front. 

"Enjoy love," That peppy exclamation was Bobby's only warning before he was sudden deep throated by an all powerful demon. His ankles crossed over Crowley's upper back and his hands went into that black hair. Of course this didn't matter because Crowley would continue at his own pace regardless of what his lover did.

For a while he just held it while slowly licking with his mouth closed and swallowing around the head as it hit the back of his throat. It was just a nice lazy blowjob to torment Bobby. Bobby was effectively balancing on his lower back with his ass as much on display and the rest of him so Crowley took his chance to knead that ass in his nice strong hands through the fabric of the briefs and it made it all the worse. Amid this all the little twitching and flinch was just a cruel punishment to Bobby's nipples as they kept rubbing against the fabric.

Still just lazily sucking he moved one hand and went to smack the exposed portion of Bobby's arse. He quite enjoyed the nice snap and the cry Bobby let out at such rough treatment. But he wasn't going to give him any time to recover so he went to town on the cock in his mouth. Setting a brutal pace of suck, licking, and still deepthrating and swallowing. Every now and again he would smack that arse again alternating which side he hit. The sounds kept growing lounder and more desperate. Thank Chuck Bobby had so much land around the house otherwise they might be facing a noise complaint. 

He kept going and going and eventually decided to go out with a bang. He smacked both sides of Bobby's arse and then moved his hands under the fabric to squeeze skin on skin. He licked around the head a few times and then went down again. The poor man was twitch and shaking and it agitated his skin with how much he was rubbing against the suspenders. It was all too much and he was finished.

"Oh yes! Fuck!" He came right when Crowley was deep throating him and he swallowed every single drop. Then he heard Crowley pop off his dick and the sound of a camera. Then Crowley tucked Bobby back into his pants and took another picture with his phone. Bobby was too exhausted in his afterglow to stop him.

"Lets get you to bed darling," and the next thing he knew Crowley threw him onto his bed on his stomach with one leg hanging off the side of the bed with his ass on display. "You know the best part about swallowing is that you don't even need to change after sex. Although I would change one thing," snap. And Bobby felt something in his ass and heard one more click of Crowley's phone taking a picture to accompany the others he took. "There perfect. Oh and don't worry about me these pictures more than make up for the case of blue balls."

Bobby mustered up all his strength and looked behind him to see a white devils tail sticking out of the back of his underwear. Not caring enough to do anything he turned his head back to his pillow and promptly passed out.

**Notes for the Chapter:**

> Next is jockstraps.
> 
> The briefs they were wearing were basically Calvin Kleins high cut men briefs but with a trapdoor in the front. And the suspenders were literally the waist band but long enough to cover their back and torso. 
> 
> Comment if you like this and if you want to see other things. I have this whole fic planned out but I'd happily take suggestion for future pairings and kinks.


	4. Jockstraps

**Summary for the Chapter:**

> They are both so cheeky and just want to torment eachother. Bobby gets smart and Crowley is enthusiastic.

**Notes for the Chapter:**

> Crowley has a ten inch dick. After all that's what he sold his soul for.

Bobby woke up to something being pulled out of his ass and something else being pushed into it. In his attempt to sit up he found out that there was a firm hand pressed between his shoulder blades and another one reaching past the waistband of his briefs to finger his ass. 

"I thought that since I never got to ruin these last night I should do it this morning so you have a reason to shower and change, because even though I love how you look and feel in these there is still so much more to try." Crowley wouldn't even let him catch his breath he continued to poke and prod constantly hitting Bobby's prostate. Eventually he went to two fingers and really started the rough treatment. By now Bobby had started to rut up against his bed in small circles. The soft briefs making it just as sensual as before. They never even got to three fingers because Crowley had decided to press his fingers right into Bobby's prostate and ground against it until he came. The sound he made was ruined and animalistic from the combination of having just woken up and the sex.

"See you tonight love. I'll be back around six." He kissed the back of Bobby's neck and disappeared like always.

Bobby laid there enjoying his afterglow for about ten minutes before it was time to get up and get cleaned. Crowley did this so he would have to shower which effectively ment he had some new underwear to try on today. Bobby decided to give his hair a break and not use shampoo or body wash today. He did shave his pits though. He really wasn't a stickler about body hair just look at him and look at who he chooses to fuck regularly, but the one place he draws the line is someone's pits. Crowley even said he liked when Bobby had a nice bush but absolutely detested pit hair. It wasnt even long but he chose to re-shave it anyway given the likelyhood of having sex later.

By the time he had toweled off and trimmed his beard it was time to see today's challenge. He padded over to his dress but instead of opening his top drawer first he instead checked the second drawer to see if Crowley had returned all his missing clothes. And there were all his shirts, pants, flannels, socks, and everything else all where it was supposed to be. Bobby was growing tired of standing naked in his bedroom and finally open his top drawer. 

Inside was every style of jockstrap Bobby could imagine and some he just learned of. He saw the standard kind he remembered from high school football the ones with the extra thick waist strap, then he saw ones that had to have deliberately smaller pouches where his dick would be covered but his balls would be on display, those had a much thinner waist line, and even still ones that at first appeared to be regular underwear but were missing the back. They all shared one common theme, they were made to expose someone's ass. 

Bobby got the extremely unsubtle message loud and clear. Crowley liked his ass. However it was his turn to take control in the bedroom and he was going to use it. But first he would need to pick out a jockstrap to wear. Each style came in multiple colors. He finally decided on a pair with a blue pouch and silvery white straps and waist band. The pouch would be just enough to hold all if him but just barely even then if he was spreading his thighs you would be able to see part of his balls. Then came the rest of what he would wear. He chose some socks that came up past mid calf and were the same color as the pouch with three matching silver lines towards the top (come to think of it Crowley probably left socks to go with each pair) and then a blueish green flannel. The goal with this was not matching colors but instead the shape and size of it. This was just about the only one that would only cover half his ass and would expose all of it whenever he bent over, he decided to leave it unbuttoned so it would show off most of his stomach and chest. Finally he topped it all off with his blue trucker cap. He went to go do one last check in his mirror. Lots of exposed hair and skin, dick being emphasis and ass on display. Bobby was ready to work.

After getting dressed the day progressed as usual. Though it did get rather cold going around in just a jockstrap, socks, and an unbutton flannel with the sleeves rolled up to the elbow so he had to turn the heat up by five degrees. He would tie on an apron to protect himself while cooking and he felt so aroused every time he sat down. Because of how short the flannel was his bare ass always touched where ever he was sitting. He should have found it unsanitary but he was so distracted. He owned the chairs in the library for years but this was first time he felt the material against his skin like this. He groped his dick just about everytime he sat down. Just from the feel of something against his ass was arousing. He had to go outside at one point to check on something and didn't even go beyond the porch because he was determined to not put shoes on. Even with the little time he spend outside it was turning him on so much. Someone could have come in for a repair job and they would have gotten an eyeful of the outline of his dick and his hairy ass.

He wished he had been more productive but at any moment his thoughts went straight to his dick. Bobby had to stop himself from getting too excited so he could enjoy the real fun tonight. 

Crowley said he would be home at 6:00 and he was never early, but sometimes he was late so at 5:45 Bobby went to practice his billiards skills. Everything was set and now he only had to wait out the clock.

....

Crowley came into the living room at 6:04 and he was thoroughly pissed off. Three demons had been killed by one hell hound. And while that was reassuring about the strength of the hell hounds it also showed immense levels of incompetence from his subjects. 

Finding no one in the living room or kitchen he went further into the house until he heard noises coming from the room with the pool table. Walking in he saw...

"A perfect furry rump!" His breathing was already ragged and he just got home. He was mesmerized by how little was covered by the flannel and then when he leaned over to take his shot it was all on display. Then the legs shifted back and forth to line up the shot and he saw it giggle and wiggle. It was all emphasized by the string of the jockstrap pushing it up.

"Stop stairing. Now get in here and eat my fucking ass you idjit." The command left no room for argument and had more southern drawl to it than usual. As Crowley approached Bobby spread his legs wider and fully leaned onto the pool table. Crowley's knees hit the floor and he dived right into licking that arsehole.

"Fuck!" Bobby had his forearms on the table and his back was arched which pressed his ass out farther. "Urugh," moans were spilling out of him as Crowley greedily licked and licked not yet breaching that hole. Even now with only licking Bobby could feel the rough texture of that beard scraping between his cheeks and after a day of smooth leather chairs the contrast was even more pronounced.

When Crowley finally decided to shove his tongue down into that asshole it made everything even better. Bobby started to turn his torso. While he was still presenting his ass he moved one hand to the back of Crowley's head and pushed him further in.

"Don't act like you need to fucking breath because we both know you don't need to." It was amazing he could even say a competent sentence while having his ass eaten out but demanding it like that just proved how much he wanted it. The licking and probing continued. At one point crowley even pulled his tongue out and sucked strait on the pucker. 

"Crowley," he moaned out between pained breaths. "I..want...to come...just from th-this," every word was a struggle but the message was clear and Crowley jumped back in with renewed vigor. He just kept going, never bothering to pull his tongue out. It seemed to stretch even deeper than before and really penetrate that ass. At that Bobby moved both hands back to gripping the table and shoved his whole body back onto that mouth. 

That was all it took and then Bobby was coming and it was going through his jockstrap and hitting the pool table. As Crowley pulled back he could already feel the burn that beard left behind.

"I didn't expect this to happen when I left behind your newest underwear. I never thought I would eat out a scantily clad redneck while wearing a three piece Armani suit." Crowley was now stand at his full height and Bobby didnt even try to move. "And to think I still haven't gotten off today."

"Well we can change that ya idjit. I may be spend but I'm still wide open." Bobby moved his hands and spread his ass to show off that ruined sloppy whole. "I can't come again but after that you're good to slide right on in."

"Well it would be a shame to waste such a gift." Crowley lowed his pants and trousers just to his mid thigh then lined up and slammed all 10 inches in all at once.

"Fuck." Things were just getting started for the night

**Notes for the Chapter:**

> Next is speedos on the beach


	5. Speedos

**Summary for the Chapter:**

> Crowley convinces Bobby to go to Scotalnd for a weekend and when they go to the beach they need to dress properly.

**Notes for the Chapter:**

> British slang  
Dinner = Lunch  
Supper = Dinner
> 
> Not actually smut but a lot of suggestive imagery and groping.
> 
> I just kept going and going with this one

If asked how he felt about this trip Bobby would tell everyone that he was annoyed and couldn't stand the spontaneous vacation. But in actuality he was pretty happy to get out of the house for once. He would have preferred something more local but he would work with what he was given. Crowley wanted to come over for some festival Bobby had already forgotten the name of and it lasted all weekend. Crowley ended up paying for a luxurious condo for them to share. It felt more like a hotel suite but either way ot was nicer than the motels he was used too. Anyway, Crowley wanted this specific place because it was apparently equal distance from the beach and mountains.

The real kicker though was that neither of them brought any luggage. Actually they just warped strait there. And considering Crowley was legally dead they were both technically there illegally, but the authorities probably had bigger problem than a couple's weekend away. But back on topic they have no changes of clothing because in Crowley's words, "Why waste all that time and space packing when I can just make up outfits." Bobby's first thought to that was that he would make them outfits that would have then arrested for public indecency but Crowley liked this place and he would probably want to come back this century so becoming a convicted felon was probably something he would try to avoid.

He was waiting for Crowley to return from something and he was currently occupied with his own reflection. Due to the insistent begging and pleading Bobby had let his beard grow out more. It was only slightly longer but it was much fuller. The area on his cheeks had filled in very evenly and it was all noticeably thicker especially in his mustache. And Crowley was doing something similar. What would have previously be called stubble or scruff was now an actual beard. Again it was still close cropped but you could no longer see the skin of his jaw through all the hair. It made them both look marginally younger but you couldn't really counter the hair thinning hair and receding hairline Bobby had to love with. 

He heard the door open and ended his staring contest with his reflection. "Good you're back. I was starting to so stir crazy by myself with nothing to do. Oh and what were you doing again?" He sat down at the table in the room and Crowley sat adjacent to him.

"I was trying to find something for us to do. The festivities don't really get going until tomorrow but I wanted to treat you to more than just one day here. Though clearly I've forgotten how simple it can be." He sounded slightly defeated and annoyed as he leaned onto one elbow on the table.

"So is there something to do or not," Bobby didn't feel like agitating him right now but he was also bored out of his mind with no work to do.

"The local options are hiking trails, sheep farms, or the beach and a little beach side shopping district. All the major restaurants in the area are closed today so they can prepare for tomorrow." Now he no longer sounded defeated just bored. "And of course there's always the option that involves me taking us somewhere else short term."

"The beach sounds nice but will I be freezing my balls off?"

"No the water should be fine and if you don't feel like swimming we can always walk along the shore and peruse the little shops they have set up there." He was starting to perk up knowing something sounded agreeable. "Do you want to wear everyday clothes or swimwear?"

"I guess swimwear. If I'm going to the beach I want to keep the option of getting in the water available," While this might not be exciting it certainly sounded relaxing and that's something he has been dearly lacking lately.

"Are we getting there the demon way or the human way? And do you want to change here or there."

"I guess the human way after all you made such a fuss about this suite being equally distance from the mountains and the beach." It seemed like a strange question to ask given his opinions earlier.

"True but it loses its charm when you realize that's over an hour each way." And now he was back to soinding defeated.

How sad was it when Bobby Singer has to be the positive one, "So we can take the demon way and we might as well change here anyway." Suddenly something seemed to cross Crowley's mind as he immediately became much more excited.

"So when do you want to leave?" He was starting to look almost giddy and coming from a demon that was absolutely terrifying.

Bobby had to think it over. It was about 9:30 and he was already bored out of his mind but how much could they really do at the beach and could that realistically last all day. Ultimately it was the ticking of the old grandfather clock that made up his mind. He was absolutely sick of the sound of it. "Let's go now before it gets too crowded and see how long we're there before we get tired of it."

"OK," Crowley responded and snapped then two garments appeared on the table in front of them.

"What are these?" There was noticeable shock in his voice. Bobby knew what these were. They were speedos and suddenly his public indecency fear didn't seem too far off th mark. He picked up the black pair examining it closely.

"Its swimwear love. And that is my pair," he snatched the black pair out of his hands and gestured for bobby to take the red ones still sitting in the table. "When in Rome do as the Roman's and when in Scotland dress as the Scottish."

"I ain't looking like an idjit in public," he was crushing the red pair in his fists.

"Trust me you won't. This is what everyone wears and honestly you would stand out more if you wore the long knee length monstrosities you Americas gravitate to." He was so confident in what he was saying and he knew he was right. Bobby knew it too.

"Alright fine." He stood up, threw the swimsuit on the table, and started stripping right next to the table. He stated with his coat, followed by his flannel and shirt. Once his torso was bare he started to undo his belt and pushed down his pants and underwear all at once (it was actually convenient he never bothered to put on shoes this morning). Everything was sitting in a pile next to him and then he heard a snap. He looked up and saw a naked Crowley then he looked back down and found his old clothes missing. All that was left were the two pairs of speedos on the table

They each grabbed their respective pair and went to put them on. Bobby was silently thankful it was plain red instead of some loud design. Crowley warned him, "You need to slowly shimmy them up your hips. Their made to be snug so you can't just pull them straight up." Bobby heeded the warning and looked to Crowley as an example. Slowly moving them up his thighs bit by bit. Its was a tedious process but after about four minutes Crowley had his on and Bobby took just a little longer. When he reached the top and realize there was a pouch on the inside for him to stick his dick and balls into, rather than overreacting he tucked himself into the pouch and could feel how he was being pushed up and out by it. They fit very similarly to the briefs where they sat high enough to cover his ass but left the sides of his rump and thighs exposed. The difference was in the front they seemed extremely low cut and some of his bush was sitting above where they sat.

"Uhm, Crowley I'm not sure this is right?" We was again worried about indecent exposure but when he looked up he saw Crowley dealing with the same issue. There was some of that black wiry hair sticking out above his speedo too.

Crowley then walked over to Bobby tucking himself under Bobby's right arm and moving his left hand over his back and onto his shoulder. "Don't worry love I've got this under control." His right hand now moved down and he started carding in through his exposed bush much like he would do as a build up to a hand job but this time he was slowly straightening it out. "You know I never understood manscaping. I much prefer my men naturally hairy all over, with one exception." Bobby knew he was referring to his pits which had just been shaved earlier that day. He was finishing up with the hair. Just smoothing it out and patting it down to wear it blended in with the hair on his stomach and it was just one big canvas of honey brown all over his body.

Crowley stepped back and started to sort himself it next but it would be significantly easier as his black hair perfectly matched the black speedo. Still straightening and smoothing it over to blend in. Looking at this Bobby's eyes were eventually drawn to the large bulge in the front if Crowley's speedo. Crowley was definitely a shower not a grower so if he was ten inches when hard then he was still a solid eight when soft and the pouch emphasizing that just seemed like pure overkill. Someone would probably think he stuffed his speedo with something because people aren't that big naturally. And to be fair Crowley wasn't that big naturally he had sold his soul for a few extra inches. Bobby was desperately trying to not get hard at this point thinking about his dick.

Crowley had finished up and could see Robert staring at his crotch. Crowley moved up towards Bobby and laced his arms around his neck. "Jealously of something?" And then Bobby felt those lips pressing against his. Their thicker beards scraping and intertwining. Their cocks pressed right up against each other and Crowley ground forward ever so slightly.

Pulling back to let Bobby breath he took his moment to break the sexual tension, "Don't we need sunscreen considering neither of us sees much of the sun?"

"Of course ever the vigilant one. But you know there is a benefit to never dealing with the sun. No tan lines to speak of." Crowley laughter at his own joke and snapped to cover them both in a light layer of sunscreen as well as making one other change.

"Now I think we're ready to go. Let me just grab onto you and we can be there immediately." Crowley moved his hands around Bobby's waist to squeezing that arse and warped them to the beach.

....

As soon as their feet hit the sand Crowley removed his hands from that fine rump and gestured out to the sandy beach. From what Bobby could see it appeared to be bookended by two rocky cliffs and stretched for at least two miles. They were standing only a few yards away from one of the cliffs and everyone was further down the beach.

"Oh!" Bobby said and stepped closer to the shore line. The water was much nicer than he was used to. It wasn't that Fiji blue that he heard about and it still had a green tint to it but it was so much better than the lake scum he grew up around.

While Bobby stepped forward to admire the view of the ocean Crowley was enjoying his own view. The word bottom was spread across that big ass in front of him in all capitals. It was in a black that perfectly matched Crowley's speedo. And he knew that across his arse was the word Top in red to match Bobby's speedo. He made the slight change when he was applying sunblock and he wasn't going to let Bobby know about it until much later.

He lightly jogged over to his redneck fish out of water. Feeling his cock and balls move from side to side in his strides. He didn't have to worry about anything popping out (they were much too tight for that) but it definitely was an obscene image that everyone was sure to give a double take. As he reached Bobby he stretched his hand out and squeezed right between the two T's on the word bottom. Bobby worked to quiet a surprised Yelp. "So what do you think?" 

"It's so blue. I've really only seen muck green water in nature before."

"Well come on there's much more to see and you can take in the view as we walk over there." He placed a hand on the small of his back and nudged him forward. He couldn't run ahead for fear of ruining the surprise but he would make due.

....

It was a change of pace having Crowley walk next to him with a hand on his back. He was used to a lack of personal space and familiar touches but they tended to be more suggestive and unsavory, so the simple public display of affection was unusual but certainly welcomed. Of course that didn't remove all his inhibitions. Having spent most of his life in small backwoods southern towns he was used to public homophobia and that fear persisted. Sensing his discomfort Crowley tried to sooth him. "Relax love. People around here don't give a fuck who you choose to shag. Try and enjoy our day out." The hand on Bobby's back had started to rub small circles into it to calm him. Taking the advice Bobby threw his right arm around Crowley's neck and rested it on his shoulder and Crowley's hand moved to rest on Bobby's hip right on top of the tight fabric. Their sides were now pressed together and they continued their slow trot up the beach like that.

The sparse passersby would often give them a double take. They were probably left in disbelief at the size of Crowley's bulge. And then when people came running up from behind them they would get a side eye. Bobby was too awestruck to notice it but Crowley wasn't disillusioned, he knew what they were looking at. They could obviously read the back of their speedos and probably found it tasteless. In response he often started rubbing where he and Bobby were connected just to drive the point home. Poor Bobby was oblivious to its actual meaning and just assumed it was his demon's usual shenanigans.

After walking for about half a mile Bobby spoke up. "So do you want to get in the water now or would you rather wait.

Crowley playfully rested his dead on that nice shoulder. "I'll get in later. Right now I just want to get some vitamin D before I'm back wear the sun literally does not shine." He pulled away from Bobby and unceremoniously plopped his arse in the sand. "I don't want to stop you from getting in now. You can go on ahead I'll join you in a few minutes."

Bobby took in the way his demon was casually leaning back on his arms in the sand. Clearly he wasn't the only one who needed the time to relax. "Suit yourself. I'll jump on in then." Bobby felt so exposed now that he didn't have that warm body pressed up against his side, but that was all the more reason to get in the water faster. He turned away and headed toward the ocean. 

The view just kept getting better and better. Watching those nice legs strut could become a hobby all on its own. The slight way that body bobbed up and down and the way the sun reflected off the little residue left by the sunscreen was hypnotic in its own right. There were far too few times Crowley actually got a good long view at that nice define back. Contrary to what you might assume from the love handles it was still quite muscular. Did he even have to mention that slight jiggle and shake he got to see with ever step. That speedo perfectly hugged that arse and left nothing to the imagination and left even less when you read what was written on the back. He was such a possessive little shit and he wanted everyone to know it. He brought his phone out of thin air snapped a few pictures and then sent it away again.

He laid back into the sand putting his hands under his head so he could still enjoy his custom made view. He stretched his legs out and spread them slightly exposing himself even more (he was truly trying to see how much he could flaunt his giant cock to the world without breaking the law). By now Bobby had made it into the water and he saw the way the water lapped against those thighs

He gave Bobby a few minutes to enjoy himself. Letting him wade in deep and actually start swimming before he joined him. He could now see Bobby bobbing up and down in the water as he did a breast stroke and figured it was time to have some fun of his own. He slowly stood up and made his was into the water. Bobby noticed and swam in to a shallower part were he could stand but the water only came up to his navel. Meeting him in the middle Crowley took a moment to find his words. He was distracted by how the water dripped off that beard and chest hair, the way Bobby was huffing from swimming, and he couldn't even see his lower body yet. "So enjoying the beach as much as you hoped?"

Bobby moved behind Crowley and wrapped his hands around that nice stomach placing his head on a shoulder. it was a reverse of how things usually went. "I was starting to get lonely. You certainly took your sweet ass time getting in the water." The snark was only superficial he was really having fun.

Crowley was just glad that water was too murky for Bobby to clearly see his arse and ruin his moment. "Yes well I'm here now so we can just cool off and enjoy each others company." He moved to lace his fingers between Bobby's hands over his stomach. He relaxed into the touch and felt a slight pressure against his arse, but that was something to deal with later.

"You know to cool off you traditionally have to get wet first."

"Well I am. At least partially."

"Well I'll speed up the process a bit." And before he had a chance to react Crowley found him self falling forward towards the water with the full weight of Robert on his back. Next thing he knew he was coming up for air and spitting out salt water.

"You cheeky little fucker!" Crowley was positively fuming as he tried to recover from the surprise. Even if you aren't a demon the the feeling of salt water in your eyes was awful, but salt can fucki f melt his skin if its strong enough so it's worse for him. The laughter Robert was eliciting only fueled his anger. "Is that the only reason you got in the water?"

"No but you took so long I decided to get even and besides now that you're soaking wet you can get on to swimming with me. The only thing that stopped Crowley from smiting him then and there was that he noticed Robert had dunked himself as well and new droplets were tracing the lines of his body.

"Fine but this isn't nearly as funny as you think it is."

....

Crowley really just spent most of his time relaxing and floating on the waves. Every now and then Bobby asked him to swim with him and he decided to indulge in it. After that he would go back to floating and watch Bobby swim away. This led to something he never even considered. When Bobby was swimming away Crowley could look between his legs as he kicked and see the way the fabric was tightly stretched over Bobby's taint. It was something he never knew he wanted but he was certainly excited to see it now.

"Love!" Crowley called as Bobby had swam a good distance away from him. Hearing it Bobby came closer and stood in the chest high water. "So it's about 1:15 would you like to get out and go grab some dinner."

Bobby was too distracted to answer because he had a realization. How did Crowley know the time? Neither of them had watches or phones on them. Hell, they didn't even have shoes or or any money to speak of now that he thought about it. "How do you know the time?"

"I looked at the sun. Given several hundred years you eventually learn a slightly useful skill. Some people choose knitting I went with becoming a living sundial. And don't worry I can make some cash appear to pay for our food so you can sample the local palette." Crowley really didn't feel like answering pointless follow up questions right now so he made his answer as thorough as possible.

"I guess we can but where would we get food?" Hadn't Crowley said earlier that all the restaurants were closed today today? The confusion was etched into his expression.

Crowley went and pointed to an area towards the farther cliff that was raised up off the sand. "That little plaza over there. All the sit-in restaurants are closed but street vendors with carts are still out and about. They also have picnic tables and benches so we wont be forced to eat in the sand." Mid-monologue he took the hunter's hand and started leading him out of the water towards the beach. 

Getting out of the water side by side Bobby noticed a problem. Both of their bushes were looking curly and wiry again from all the activity and moisture. "Crowley?" He only needed to say his name and look down to indicate his problem.

"Don't stress we can just do like we did this morning," They both moved further up onto the sandy shore and then he indicated for Bobby to sit down when his ass hit the sand Crowley started kneeling and getting in his personal space in the same manner as earlier in the day. He got to work smoothing and straightening that hair out again only this time it felt much slower and much more sensual. He could feel every slight tug and nudge on the sensitive hairs. And he was touching such an intimate area in broad day light with dozens of people around to see him do it. It all added to Bobby slowly growing hard in the speedo but before he could reach full mast he felt Crowley pat the hair down and shift back to himself without leaving Bobby's side. He seemed to be much less interested in teasing himself the way he had with Bobby. But now that he was soaking wet Bobby really noticed how that hair was the exact color of the speedo. It was so tight and the hair was so thick at the base it blended perfectly and as it slightly lightened up towards his stomach it looked to fade right into his skin. It did the same thing moving down his legs as well.

Crowley was the first to stand up. After wiping away the excess sand he offered Bobby a hand which he gladly took. "So lets head on over," He took that rough hand in his and started walking towards the plaza. Bobby went and brushed the sand off his ass then grabbed that hand and started walking again.

....

The stroll was just as nice as it had been before. With simple hand holding. While the overt suggestive groping Crowley usually went with was nice he decided to do something more mundane after teasing Bobby in the sand. The walk was much longer which meaning significantly more people passed them by. Crowley noticed every second glance and side eye they received, while Bobby only noticed how many other people were dressed like them. Usually what they had on was less revealing but it was still a brief cut so it helped his confidence. 

After about thirty minutes of walking they made it up the stairs to the plaza which appeared to be much bigger up close. It had to be at least the size of a football field. Spread all around were tables, benches, little carts selling desserts and snack foods, and a shack that was selling real food (like fish and chips as opposed to soft pretzels and shaved ice) and beer.

Crowley tapped his shoulder and held his hand out. "Here's a twenty pound note it should be enough to get food for both of us and a beer for you. If you've got any change left over just tell them to keep it. You can get food from wherever and just meet me on a bench over there," he said and pointed towards some open benches on the opposite side away from the shack.

The two split off in opposite directions. Bobby figuring that he might as well get real food since that line was no longer than any other line. While waiting to place his order he could feel eyes on him but he couldn't tell from where. Once he was about half way through he heard some drunks whistling and cat calling.

"Hey Honey I'll pay for your food if I can feel you up."

"Do you charge or is that arse for free?"

"We'd gladly tag team you if that's what you're into instead."

"Is all that natural of did you have some work done to look this good?"

"Care to meet me in the bathroom so I can see more of those nice big thighs?"

He turned and saw the poor woman they kept cat calling. He got out of line and went straight up to the clearly drunk 20 somethings. "Listen up you pieces of trash leave her alone and get out. My god what kind of shithead gets piss drunk at 2:00 on a Saturday."

"Sod off you old coot. You're just some rich guys bitch. I bet you don't even have a cock." The head asshole was too proud of himself for that pathetic insult.

"Big talk coming from a limp dick asshole. Who probably got cut off after his third drug addiction."

"Shut up you senile old--"

"Stop and just go home and when you get there tell your parents I'm sorry that they had to deal with you for 25 years before they finally decided to kick you out." Him and his two fellow assholes started grumbling and slowly walking away. Bobby made sure the woman was okay and was lucky enough to be able to get his old spot in the line.

By some miracle he made it to the front, ordered, and got his food all without having to make any threats of castration. He scanned the place and found Crowley sitting on a wooden bench with his legs spread and his arms hanging off the back. And the bastard had the nerve to call him a whore when he sat like that in public. Regardless he slowly made his way over to him, trying to avoid running into someone.

"Finally got our food and I didn't injure anyone in the process." Crowley scooted over slightly to give Bobby space to sit but he made no inclination to close his legs. As he was sitting down Bobby handed him his food. 

"Fish and Chips. I don't know what I was expecting but then again when eating at a beach shack you don't have many options," Crowley moved to take a bite and Bobby opened his beer (it was some brand he never heard of) and took a sip.They sat there in relative silence as they ate until everything was finished and Bobby went to throw their trash away. 

"That beer was surprisingly weaker than I was expecting." Not the best way to start a conversation but he figured they'd be sitting for a while to let their food digest.

"Why do you say that love?"

"There were some drunks harassing a woman over by the that shack and they were somehow shitfaced at 2:00 in the afternoon. Then they called my a rich mans bitch and I was more than happy to ruin their pride."

"No, it just seems like they are all light weights. And they don't know when to leave someone alone who's clearly better than them. Maybe I'll properly educate them."

"Don't be an idjit. Do whatever it is you plan on doing, do when we're back home okay." Bobby knew fully well that Crowley would smite them right now and raise hell if he let him. 

"Okay love. Only cause I can't resist you." He stood up and walked over back towards the beach. He had his good fun so now he would just wait and see how long it took Robert to notice his little change in wardrobe. "I feel like soaking up some more sun and really getting my back now."

Bobby Followed behind him and only now did it occur to him that he never got to see Crowley's ass today. They had always been walking side by side or up to their waists in water. He took this moment to enjoy the way those calves flexed with each step, those nice biceps that were deceptively strong even with the demon powers, and how that nice dark hair peaked over his shoulder and side onto his back and disappeared into that speedo. God is that what his ass looks like? It wasn't riding up but it still clearly defined his ass perfectly and left so much of it exposed. Bobby knew there was a lot to see but he never knew it was quite that much. Only now did he notice the world TOP written in all caps wright across the center of the back of it. He didn't remember seeing that on them back at the suite (God that felt like so long ago) but decided now wasn't the time to question it. He was still a good ten paces behind Crowley and he was contemplating staying back there to enjoy the nice shake he saw with each step.

Crowley found a nice spot that wasn't too crowded and had nothing obstructing the sun. He laid down on his stomach and crossed his arms to rest his head. Bobby just stood observing for a moment. The way that ass was stick out so much. The tight stretch of fabric barely managing to cover his taint. And because this was Crowley he spread his lags wider than necessary and bobby could see how that monster dick was being push down as well. Bobby laid down in the sand and took the same position spread legs and all. He was occasionally dosing off with Crowley periodically reminding him to roll over so he didn't burn.

They had just rolled onto their stomachs for the third time and bobby finally decided to pop the question in his head. "Hey, Crowley. Why does your speedo say TOP on it?"

Crowley turned his head so they could face each other. "Because your's say BOTTOM and everyone needs to know who your top is. To clear up any confusion they've been like that since we got to this beach so now everyone is privy to what you do in the sack." He had enjoyed his fun while it lasted.

"Huff, you know what fine. I'm too relaxed to be pissed off at you and its not like I plan on seeing these people ever again. Just make sure to leave it there so no one misses the message of how my ass belongs to. But just so you know when we get back I'm giving you shit for this."

"Okay Love." Crowley reached out a hand and squeezed the arse cheek closest to him tightly. Since Bobby knew about his secret Crowley might as well be as lewd as was legally allowed. Even after he stopped squeezing it he moved his hand to be just inside the hem of the speedo all four fingers just managed to fit inside the tight fabric along with that arse, he was enjoying the possessive touch and there was no room for confusion now. This had turned out better than expected and he knew that no matter what happened he would certainly enjoy it.


	6. Commando

**Summary for the Chapter:**

> Do I really need to explain this one.
> 
> This is like one step away from Crack

Once they got back from the beach the first thing Bobby did was push Crowley onto the mattress and crawl on top of him. His knees were on both sides of Crowley's waist. Their twin bulges were lined up, stomachs and chests pressed together. Bobby's hands in Crowley's hair and Crowleys hands roaming over Bobby's back. They were both still in their speedos and Bobby started grinding down against that thick girth of Crowley's dick. He went straight to conquering that mouth, going for full body contact. Bobby's nipples were being tickled by Crowley's soft chest hair and Crowley could feel their bushes rubbing and getting tangled together. Ruining all his work to straighten them out and adding another point if delicious stimulus.

The kissing was a messy battle for dominance with Bobby trying to come up for air as little as possible. When he came up for air again Crowley took the opportunity to place both hand on the center of his back and push down. This caused Bobby's legs to slip and slide farther apart but more importantly it led to all of Bobby's weight falling onto him. He could now feel the full force of every single movement all along his torso. 

They were both grinding at completely different rhythms that matched their own desperation but seeing as their dicks were shoved right up against each other with 270 lbs. of Bobby pushing on them, rhythm didn't seem too important anymore.

Bobby broke off their messy makeout to leave a hickey on Crowley's shoulder. While he was just biting and sucking Crowley looked over his back and saw that red clad arse gyrating in desperation. It was one thing to feel that arousal and another thing to see it encompassing his entire body.

"Gah!" Bobby drew blood on that last bite and Crowley moved his hand onto the back of Bobby's head to hold him there as his other hand kept his body down. He could feel every single time those nipples rubbed against his chest hair. He knew how close his lover must be because he was right there along side him. With one last burst of strength they both started rubbing as fast as they could culminating it two loud broken moans of relief. 

They both relaxed and those hands started stroking hair and rubbing smooth circles into backs. However Crowley was going to have to break this news eventually and after seven minutes to relax it seemed like the right time.

"Because of the material their made of all your cum is just stuck inside your speedo. You have to change or you're going to be stewing in it all night." He continued to rub slow circles into that back as he said it. 

"Its going to take like ten minutes to get these off and I'm not up to that challenge right now." He pulled his head up just enough to look him in the eyes. "Could you demon magic us into something else."

"Of course," he was far too pleased by such a simple request but then Bobby suddenly felt much less sticky and his ass felt a lot colder. He rolled off of him and saw that they were both in white jockstrap. They were the same kind as in high school. A three inch thick band and an overly generous pouch, but just as Bobby expected Crowley still managed to completely fill it out and then some. It wasn't just that Crowley had a big dick but his balls were proportionally huge and he could see part of those balls peeking out of the sides.

He rolled over to face away from Crowley but the king of hell followed him. He move one arm over and one arm under Bobby. Putting one across his stomach and the other across his chest making sure to be on top of both nipples. Crowley's front was right up against Bobby's back and he could feel where that clothed dick was shoved right between his exposed ass cheeks. That dick was actively pushing his cheeks apart so it could lay between them.

"Don't try anything." He attempted to muster up a threat but he was too tired for it to be very effective. 

"Wouldn't dream of it. Now get some rest we have plans tomorrow." He placed a kiss on the side of his neck and then went silent. Sleep soon followed for both of them.

....

"No."

"But..."

"No!"

"Please this is the whole reason we came here. It would be a waste to not seize this opportunity."

"You can seize this opportunity yourself. I'm not going out without underwear." Crowley actually expected him to go out in a kilt without any underwear on. The demon must have finally snapped from pressure to think he would go along with that.

"But its tradition. That's the intended way of wearing them." He was full out begging and pleading by now. And when appealing to his humanity didn't work it was time to tackle it the demon way. "How about we negotiate?"

"And why would I do that?" He was crossing his arms now.

"Because if you're so sure where you stand then you won't have to worry about changing your mind." He loved toying with people when making a deal. It may have been bad to do it to Robert be he'd been planning this for weeks so he wasn't going to give up easily.

"Fine what do you have to sweeten the deal?"

Coming up to Bobby he leaned against him and started stroking his face. He brought his lips right up to his ear and in his most seductive voice made his offer. "How about I let you eat me out to open me up," that earned him a poorly veiled huff. "Then I let you shove a nice six inch long plug up my arse to keep me open. Then I put a matching plug in your arse with my powers to save on time."He was now panting in labored breaths. "Then we put our kilts on so were even more exposed than we would normally be in them." His poor face was burning a bright red now. "And then we keep them in there all day so that the moment we get home we can pull up our kilts, pullout the plugs and be good to go. Sound like a better deal love?" He shifted to sound so innocent at the end.

"I fucking hate you sometimes." His voice contained nothing but venom but Crowley knew he won. "With one more condition. They need to be the plugs that lock into place so we can't remove them in the middle of the day."

"That will be fine. So when would you like to get started" it was made worse because they were both still just in their jockstraps from the night before.

"Let's start now so we aren't late." He hooked his finger inside the waistband of Crowley's jockstrap, "Drop these and come straddle my face. We should start going commando now." Bobby had already discarded his on the floor and was climbing into the center of the bed.

Crowley climbed in after him. He kneeled with his shins resting on the sides of Bobby's head. His back to the headboard and his arms stretched out along it. He slowly lowered himself until he was just above that nice mouth. His cock and bollocks were drooping onto that chin due to their sheer size. Then there were two hands spreading his arse wide and that tongue dove right on in. 

He didn't even bother with licking or trying to build up anticipation. No, he just had to go straight on in. At the very least it saved them some time. He could feel the burn of that thicker beard already. This was one of the reasons he pushed Bobby to grow a thicker beard. It turned a rim job into an experience your whole arse felt long after it was over. As it started scraping against the hair on his ass and it just got better and better. 

That sinful mouth pulled off so Bobby could breath and then came back by sucking on his hole. The old fucker was doing what Crowley did when he was eating someone's ass. It still felt good (after all that why he did it) but it stung feeling your own tricks used against you. 

When he was breached again his who body arched into it, his arse was pushed down, and his chest was displayed outward. He started moving up and down really feeling it. But just like that it all stopped.

"All done darling. Let's plug you up." Bobby sounded much too smug for a man with someone sitting on his face. He then felt hands on his back pushing him down shifting them into a 69 position. "So where's the plug darling?" Crowley managed to make two plugs with matching keys and a large 32 oz. bottle of water based lube appear next to them on the bed.

Crowley picked up the bottle and spread some lube on his fingers and started working them inside. He did this a few more times to really get it slick. "It needs to be nice and good to go so I can slide right in after I pull out the plug." Eventually Bobby got tired of the slow process and just shoved the nozzle into his ass and squeezed. 

"Urugh," Crowley was speechless as the sudden cool substance entering him. Bobby kept it up until about half the bottle was empty. He knew if Crowley stood up now it would all drip form his ass. He generously lubed up the red plug as well. He chose to slide it in all at once and used the matching red key to lock it in place. Crowley groaned as the base swelled inside of him preventing him from pulling it out without hurting himself.

Lazily Crowley got up off the bed and with a slight limp turned around to tease Bobby. "Roll over onto your stomach." His voice was strained but the authority was still present. Bobby rolled over as instructed seeing no reason to argue as he already had his fun. 

Crowley got back on the bed and sat on Bobby's lower back facing his arse. The position wasn't the best given the plug recently shoved up into his own arse but he was making it work. "Can you pass me the lube?" Bobby went to move the half empty bottle of lube but suddenly it was just empty. And now he could feel something sloshing around in his ass. The bastard made sure he knew that exact moment he got 16 oz. of lube shoved up his ass. Since there was no lube left Crowley took the blue plug and slowly worked it in past the rim. Easing it in ever so slowly. Lubing it up along the way but not letting a single drop slip out. He then took the blue key and twisted it to lock it in place. Bobby sounded even worse off because he had his arse stretched all at once unlike Crowley. They both slowly got off the bed and put their respective keys I side the little pouches on the outfits set out for them. They were both stuck like this for the rest if the day.

"Now then love, let's get ready to go out.


	7. Kilts

**Summary for the Chapter:**

> They go out on the town to very unusual effects.

Once they were fully dressed Bobby truly realized how elaborate the outfits really were. He had on a standard tee shirt but then over that a dress shirt with a ruffled front, a vest and a suit jacket. That didn't even begin to cover the lower body which had white stockings? socks? hose? All that really mattered was that they were perfectly white and hugged his legs tightly up until the stopped at the knee. and on top of those were pristine black leather square toed dress shoes.

The kilt itself was an entirely different story. It had layers and straps he initially didn't know about. According to Crowley each one had its own specific name but he had already forgotten all of them. Then there was the odd fur piece and the pouch that was on it since they had no actual pockets. It was all in a nice red plaid pattern that was similar to a flannel he would normally wear. Though he noticed it was quite convenient that it was made of several layers of thick material so even if he had an erection for the entire day no one would be able to tell. Crowley had also taken the liberty to style and smooth his hair back and then gave Bobby some beard come to use. These last few things seemed like pure overkill but it was just for a day so he would be able to manage. 

He had just worked the last of the beard cream in in and actually liked how it made his face look less bushy and unwieldy. It smoothed it our without looking greasy and it helped add to make it fuller than it already was. Exiting the bathroom he saw that Crowley had done many of the same things to himself. He was dressed almost identically except he was in a green and blue kilt instead and as Bobby entered he stood up straight looking perfectly groomed and even more immaculate than usual.

Bobby saw his jockstrap of the floor and quickly got it up his legs in the moments Crowley was looking away from him.

They now both stood in front of each other and gave the other a once over. "I always knew you would look gorgeous once you got cleaned up but I never knew it would be this wonderful." Those eyes took on a red glow and a predatory stare before quickly returning to normal, "And the best part is you look so good no one will even know that right now your arse is stuffed full of a nice big plug." Bobby stopped Crowley from squeezing his ass by smacking Crowley's own. Of course he almost seemed more happy than annoyed by that. "Oh look at that the old dog finally learned a new trick. How lovely." Now the demon was moving towards the door, "Come along now. We will be able to walk to the festivities from here." Bobby started walking and was starting to regret his decision of agreeing to this deal. When they were inside he could take short steps and scuttle about to avoid jostling the plug but now be would be forced to go out and that meant taking larger steps that would move the plug more and more against his insides. But this also meant that Crowley was in the same boat as him so it was really just a test of stamina.

Bobby was jaut a step from the door when Crowley turned around and slipped a hand under the front of his kilt, working his way up until he came I to contact with Bobby's covered cock. "Now, Robert I thought we had an agreement here."

"Shit."

"You agreed to the deal. Now drop it to the floor."

Bobby reached his hands under the sides of his kilt and then slipped the jockstrap he'd grabbed of the floor when Crowley wasn't looking down to the ground. Crowley managed to snap several photos as it made it's way down his legs. The whole concept was so arousing and he was almost happy Robert tried the trick be ause the image he made of lowering it was perfect.

"There much better."

When Bobby stepped outside into the sunlight he was greeted by the cool crisp air and immediately closed his legs when he could feel the breeze blowing under his kilt. He really was exposed as he stood there on the step to their little home away from home he couldn't possibly go out around other people like this. Crowley was further down the path almost to the gate when he turned and came back to stand in front of Bobby. He took note of the way the kilt swung to and fro with every step Crowley took. 

"Something the matter love?' There was real genuine concern in his voice and Bobby was both touched and put off by it.

"How do you walk around like this? I can feel the breeze in places where its not meant to be? And why is it so cold today? It was almost ninety degrees yesterday and it feels like its barely sixty now." God in this moment he felt more pathetic than when he was forced to sell his soul to try and get a leg up on the four horsemen.

The look of concern Crowley had turned into his usual playful, mischievous smirk. "Unfortunately you're just going to have to get used to the feeling of wind on your cock. As for the weather, that just happens. One day it will be warm enough for the beach and the next you'll need a coat and scarf. I figured you would understand coming from the south where the weather tends to be bipolar." Crowley went up and but a hand around him to lead him away.

The gesture should have been comforting but it only reminded Bobby of the trick Crowley pulled yesterday. "I swear if you have something lewd or suggestive written on the back of my kilt i will cut off that dick you sold your soul for. He said it just loud enough for only Crowley to hear. Even though he didn't see anyone else around he had learned not to take chances.

"I would never use the same idea again so soon and besides I care about this much more than the beach I wouldn't ruin it with play ground antics. And why do you care about it now yet, when you found out about my little surprise yesterday you just wanted me to leave it?" They had just exited the gate at the front of the little "yard" that came with their suite.

"I didn't mind then because it was already too late, everyone had already scene it and it may have drawn more attention if the words were suddenly not there anymore. Also it was the beach. Just about everyone looks like an idjit at the beach."

"Okay well don't worry I don't have any shenanigans planned for today that you don't already know about." His hand drifted a little further south to rest right on the top of bobby ass.

They continued their walk and could start to hear the sound of music and the murmur of a crown down the street. Then stalls started to pop up and they could see signs indicating that the road was closed for the day and that they would need to turn off onto a side road soon. Going further in they were met with rows upon rows of stalls in a large grassy park. If the stalls weren't selling trinkets and overpriced food then they were selling different kinds of scotch. There was certainly a wide variety to choose from all ages. From just brewed that day (it seemed more like a novelty than an actually good drink) to twenty years old even though scotch hardly changed as the years went on. Even more than that they saw signs advertising honey flavoring or seasoned with fruit extract, and one particular one that boasted being mixed with peppers (again it seemed to exist more for the novelty and less for being a descent drink).

Every stall had one think in common though...free tastings. They went from stall to stall trying every kind they could get their hands on Taking advantage of one of the few benefits of looking old, never have to show your ID. They first went to the one with honey and it was quite good; Crowley even went so far as to say he might come back to buy a whole bottle of it. Then they went to the 20 year aged stall and they were both thoroughly underwhelmed. It was by no means bad but when you choose to advertise the age of it and then sell it at a marked up price you should at least taste better than the standard stuff you could buy at a store. Next was the same day brewed stuff. Expectations were as low as possible and still it was disappointment. Bobby barely choked his down and Crowley spat his on the ground; That earned them a look of disgust from the man running it. They were sure to quickly walk away from him.

"Why did he look shocked when you spat it out? The stuff tasted like filtered rat piss."

"Maybe he's never had a drink so he doesn't know any better. That's the only reason to charge someone for that shit."

Bobby grabbed his hand and led him over to a group of stalls all advertising different peppers being mixed in. Next to the five stalls was one that advertised cold milk and water to those who needed it.

Crowley noticed it was 4 pounds for one glass. "Whoever thought of that stall needs to join me in hell."

"You can go and make deals after we've burned our mouths." Now they stood in front of the first of the stalls all conveniently ordered from mildest to hottest with the milk seller at the end.

They each got the small sample cuts and threw them back. "After the rat piss we had earlier I'm just glad to have a well made drink."

"It was fine but I could barely taste the spice in it. So I guess were onto the next booth then." Bobby nodded and they walked the whole three feet to get to the next stall. Now they instead took turn taking their small glasses of Scotch. 

Crowley went first this time, "Hmm, it's good but, oh, you feel the spice more as an after taste than anything else."

Bobby follow suit and came to the same conclusion, "That's...unique. I prefer my drinks to burn when they go down not after." moving onto the third booth in the row Bobby downed his before Crowley even got his hands on the little paper cup. "Oh, that's nice it burns just as like the regular stuff but a hell of a lot stronger."

Crowley took his shot. "It is good but I wonder if they have a sweet pepper one. Are you okay love." Bobby looked a little woozy and Crowley went to put a hand on his shoulder to steady him.

"I'm fine but I should probably stop before I go too far and embarrass myself in public. Maybe we should go it sit down somewhere." He was looking to Crowley for guidance right now.

"There should be some benches and tables right over here where you can rest." This time he chose to lead Bobby with a hand on his shoulder to keep him steady. but when they approached the empty bench they encountered another problem. Bobby didn't know how to sit down in a kilt. Crowley let go of him for one moment and went to set an example. "Like this love." He then casually smoothed his hands over his ass to make sure it was between him and the bench. Bobby follow his example with much less grace and subtlety. And that was the exact moment he felt the pressure on the plug. In all the excitement of free booze he had completely forgotten about it and now he couldn't think of anything but it.

He tried to calm his rapid breathing and shifted how he was sitting slightly more off center. His conflicted with his modesty as even though the kilt was long enough that it fell between his legs covering him completely he still kept his legs pressed close together for fear of accidentally flashing someone.

"Would you like me to get you some water and a pain killer."

"Yes, please." He still felt a little woozy and the plug was not helping him focus."

"Alright I'll be back in a little bit. Just stay here and don't go anywhere." Crowley then got up and started to walk over to where a bunch of food stands were set up.

Bobby relaxed into the bench trying to ignore the feeling of the plug in his ass. He started taking deep calming breaths. Eventually he closed his eyes and let the white noise of the crowd wash over him, it mixed with the feeling of the crisp air in his lungs and he was able to mostly ignore it now. He almost missed the sound pf the footsteps approaching him and it took him until Crowley was already sitting down again to open his eyes. 

"Well you certainly look like you're feeling better than you were before." Went to hand Bobby the bottle of water while he opened the little packet of pain killers and then handed him those as well. "That should at least help with the headache you'll be feeling in a little while." 

"I really don't get it. I usually drink more than this on any given day so whats the issue." In His attempt to comfort him bobby moved right next to him put an arm around his shoulder and to Bobby's utter amazement he crossed one leg over the other at the knee.

"Its because its all stronger drinks. You may effectively live off bear but that a much weaker drink so having all of the little samples today slowly added up." He stared rubbing the shoulder that his hand was on.

"How can you sit like that knowing full well you don't have anything covering you?" He had to know because so far it seemed like Crowley might be drunk as well.

"Well if they look at me now they would only be able to see part of my arse, and while that's certainly not the best thing for my public image its not really anything that wasn't on display yesterday at the beach." He went and tapped Bobby on the nose. "You don't need to worry so much besides people tend to learn not to look down if they don't want an eye full, also when I sit like this I can't even feel that plug you pushed up inside me this morning."

Bobby almost choked as he finished up the bottle of water. He needed to stop letting the demon surprise him like that or he would just keep doing it to see his reaction.

They stayed where they were on the bench for a while longer and made small talk about nothing important and taking in the atmosphere of the festival. Eventually they got up and returned to look around at what there was to offer. They had very slim pickings when it came to non-alcoholic choices, there was always food but neither of them were really that hungry and seeing as they had no need for a large carved wooden statue of a trout there weren't many stalls that appeared to them.

"Hey how long have we been out here for?" Bobby popped the question as they walked away from the fifth wood carver they had seen today.

"A little more than four hours. Why? Did you want to start heading back?"

"Well there isn't really much to do and in my old age I can only do so much walking?" They both knew he could keep going for a long while. He had build up a lot of stamina from going on so many hunts but Crowley understood that he still got tired and was at least a little bored.

"I'm perfectly happy to head back especially with what I know is waiting for me when we get there." He again moved his hand down onto the top of Bobby's arse and Bobby did the same to him. The gesture was promiscuous and somehow still just subtle enough for them to get away with it in public. The walk back was silent but the wind had really kicked up and so their kilts really started flapping about. Crowley took special notice in how Bobby walked with his legs pressed tightly together. How would he have reacted know that with one particularly strong breeze Crowley's kilt was blown up enough to expose the head of his hard cock; the man would surely turn a lovely shade of pink at the revelation.

Walking through the small lawn area and up the steps Crowley just managed to open the door before he felt Bobby push him in and shove him against that now closed door. He started kissing and claiming that mouth possessively and tried in vain to cop a feel through the thick material of the kilt. He decided to temporarily break off the kiss so he could reach further down and pull out that big dick.

"God, have you been hard all day today," He rushed it out in the short moment he needed to come up for air. They continued on teeth biting lips and fighting for dominance, tongues intertwining and exploring the others mouth. 

This time it was Crowley how broke it off, "No, just since I sat you down on that bench and knew exactly how you were feeling, and how you refused to move too much because you were scared someone might get a glimpse of your cock." Bobby tried to go in for another kiss but the hand on his chest stopped him so he could finish his thought. "Look I love snogging with you more than anyone else but I've been ready to go for over an hour so how about we make good on that promise to pull these plugs out."

Bobby went to grasp that face and feel that roughed up beard in his hands, "Then we have to figure out whose doing what." He pressed their foreheads together and they simple breathed for a bit. Crowley moved his hand up over Bobby's.

"Tell you what love, I'll let you fuck me if you agree to keep that plug in while we do it." It wasn't the same as getting to ruin that nice arse but the mental image alone would make it worth it in the end. 

"That'll work.' In one motion Bobby pulled back and slammed Crowley against the door, making sure to keep one hand firmly pressed between his shoulder blades to keep him there while he dug for the key in the little pouch. Once he found it he moved the hand from his back to lifting up the kilt so he could see as his other fitted the key into the small whole at the base of the plug. When he turned the key he heard Crowley groan as the pressure around his rim was removed. Bobby quickly pulled with plug out with the key still inside, dropped it onto the floor beside them, and moved his dick inside all without a single drop of lube falling out.

"Aw, fuck." 

Bobby started off fast, he would have loved to make it last but he'd been on edge for hours just like Crowley. They could always be slow and sensual some other time, but now was when they would be rough with one another. It was made even better because each time he thrust he he unintentionally clenched down on that plug and it was like getting being on both ends of sex at once. He was starting to understand the appeal of a three way. 

He pressed his left arm against Crowley's back and then moved his right arm down to start jerking him off. When he got his hand inside of the front of that kilt it was so damp and moist he was turned on even more. He started stroking in long hard movements, always making sure to twist around the head because when he did that Crowley would clench down on him. He kept it up until he heard nothing but short pants form the demon and he went to just circling the head as the thrust in. His efforts were rewarded with Crowley cumming against the fabric of his kilt and clenching down so tightly that Bobby was finished as well.

With them both enjoying their afterglow and Crowley was still pressed up against the door Bobby pulled his slowly softening dick out and got the plug off the floor. He then shoved it in without a heads up and locked it into place. When Crowley looked over his shoulder to give him an evil eye it was time to make another deal. 

"If you keep it in you can fuck me later tonight with the plug up your ass. And then after that you can plug you cum in me as well and we can sleep like this all night." 

"You won't be able to walk tomorrow."

"I'll hold you to that."

....

After they got home the next day Bobby woke up alone and went to take his shower. Once he got out he placed his towel around his hips and went over to his underwear drawer. When he opened it he saw boxers, briefs, jockstraps with matching socks, and even speedos, but not a single pair of bus old underwear.

**Notes for the Chapter:**

> And so this story draws to a close. Please comment if you have suggestion for future fics or criticisms.

**Author's Note:**

> This has no benefit to society


End file.
